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If this scenario is actually possible then it seems like the reason should be that the thing dropped from higher up gets to accelerate faster at first due to the thinner atmosphere. However, I've tried quite a lot of toy examples with different dependencies of air resistance on height and on speed, and none of them showed the trailing object ever quite catching up; unless I've screwed up or there's some other thing going on (relating perhaps to the earth's magnetic field or solar wind or something, but these seem like desperate longshots), either this doesn't actually happen or it happens only when the circumstances are just right.
It should always happen, when there are no extreme conditions which would prevent it.